Oakland Vacations from $131
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Save 100% on your flight
per person
Nov 10 - Nov 12
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Great hotel, great area, but could’ve been cleaner. Shower ceiling also had peeling paint. Hotel staff and valet was very friendly.
Reviewed on Aug 15, 2025
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Save 100% on your flight
per person
Nov 10 - Nov 12
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8/10 Very Good! (2,979 reviews)
Convenient place to access stadium for games. Nice view of river
Reviewed on Aug 16, 2025
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Save 100% on your flight
per person
Nov 10 - Nov 12
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.4/10 Very Good! (1,334 reviews)
Bike rental was fun. Friday night restaurant was closed at 9:45 pm when advertised to be open until 10.
Reviewed on Aug 15, 2025
Kimpton Hotel Monaco Pittsburgh by IHG
Downtown Pittsburgh
Save 100% on your flight
per person
Nov 10 - Nov 12
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,205 reviews)
The staff is very friendly and accomodating. I love the hotel decor and offerings.
Reviewed on Aug 16, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Aug 24 to Aug 25
$148 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (405 reviews)
"Conveniently located, very friendly and helpful staff, comfortable beds (uncomfortable sofa bed!), Internet access good. The restaurant could have more variety of options"
Reviewed on Aug 16, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive, Pittsburgh, PA
Fully refundable
$127 nightly
The price is $145 total per night from Aug 24 to Aug 25
$145 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Great room, terrific bar staff, convenient to University. We had a great time!"
Reviewed on Aug 10, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Aug 31 to Sep 1
$214 total
Aug 31 - Sep 1
Total includes taxes and fees
9.2/10 Wonderful! (676 reviews)
"I travel quite a bit but this one really impressed me!"
Reviewed on Aug 16, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Private City Kickstart Tour: Tokyo
$135
per adult
100% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.